218435-20-2

Upstream product

• 6638-79-5 N,O-dimethylhydroxylamine*hydrochloride 
• 218435-19-9 (4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[(R)-1-(4-methoxy-benzyloxy)-ethyl]-tetrahydro-pyran-2-one 
• 218435-12-2 (2R)-2-[(4-methoxybenzyl)oxy]propanal 
• 218435-13-3 (5R,6R)-5-Hydroxy-6-(4-methoxy-benzyloxy)-3-oxo-heptanoic acid methyl ester 
• 218435-14-4 (3R,5R,6R)-3,5-Dihydroxy-6-(4-methoxy-benzyloxy)-heptanoic acid methyl ester 

Downstream Products

• 218435-23-5 1-[(E)-(1R,2R,4S)-7-Bromo-4-(tert-butyl-dimethyl-silanyloxy)-1-methyl-2-(2-trimethylsilanyl-ethoxymethoxy)-hept-6-enyloxymethyl]-4-methoxy-benzene 
• 218435-22-4 (3R,5R,6R)-3-(tert-Butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5-(2-trimethylsilanyl-ethoxymethoxy)-heptanal 
• 218435-24-6 1-[(1R,2R,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-2-(2-trimethylsilanyl-ethoxymethoxy)-hept-6-ynyloxymethyl]-4-methoxy-benzene 
• 218435-21-3 (3R,5R,6R)-3-(tert-Butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5-(2-trimethylsilanyl-ethoxymethoxy)-heptanoic acid methoxy-methyl-amide 

Relevant academic research and scientific papers

An approach to the synthesis of the C(17)-C(27) fragment of bryostatins

The organolithium reagent generated from the vinyl iodide 8 reacts with aldehyde 13 to give a mixture of the anti- and syn-silyloxy alcohols 14 and 15 together with the regioisomeric syn-silyloxy alcohol 16, ratio 14 : 15: 16 = 4 : 1 : 1. The major anti-alcohol 14 was taken through to the methoxyacetal 27 so confirming this strategy for the stereoselective synthesis of the C(17)-C(23) fragment of bryostatins. The diol 30, which has configurations at each of its three chiral centres corresponding to the C(23)-C(27) fragment of bryostatins, was prepared in two steps from the aldehyde 28 and converted into the vinylstannane 45.